Photos Courtesy of: Precious Pics White Glove, Syd Marks, Laura’s Focus Photography, Crystal Finnegan Photography, and Arbor Lane Studio
Everyone says your wedding day goes by in a flash. One of the happiest days of your life, surrounded by your family and friends, with the love of your life, is over in the blink of an eye. Most couples can bask in the fun, excitement, and love of the day forever. So, why not extend all that love and fun of a wedding into a multi-day event?
The Staycation Wedding Weekend
Think about them as destination weddings that are a little closer to home. Staycation weddings are mini-vacations centered around a wedding date. Guests come a few days earlier, stay a few days later, and often lodge in on-site accommodations.
For Samantha and Brandon, who had a September wedding at the Inn at Huntingfield Creek, it was also about creating a special atmosphere for guests. “We wanted them to be able to enjoy the weekend and make a vacation out of it rather than [have] a quick one-night stay.”
It’s a way for the couple to be surrounded by their loved ones and extend the celebration past the traditional ceremony and reception. Plus, they offer downtime and opportunities for casual gatherings outside of scheduled events, leading to more memories that everyone cherishes.
The More Events, The Merrier
Many couples kick off their wedding weekend with a welcome party for their guests. Typically held after the rehearsal dinner, it features cocktails and light bites where guests can casually stop in, greet the couple, and spend time together. “That was a perfect way to start the weekend and welcome all of our out-of-town guests!” says Gabby and Parker of their welcome party for their September wedding at Brittland Estates.
But this is just the start of a weekend full of fun events, whether they’re structured and planned or not. “Our guests swam, kayaked, and enjoyed the on-site sauna and plunge pool. They also went sightseeing on bicycles all around Tilghman Island. In town, many of our guests enjoyed the Oyster Festival and walking around the charming shops and side streets,” explained Janeen and Todd, who hosted their wedding at Wylder Hotel Tilghman Island during the coastal town’s famous festival in October.
Some couples might offer activities for guests to do during the weekend’s downtime. Wine or beer tastings at nearby wineries and breweries. A round of golf or a scenic hike during the day. Maybe a cooking class or a boat charter. Back on-site, couples might host movie nights, cookouts or barbecues, and pool parties, depending on the venue’s amenities.
Janeen and Todd ended their first night by the fire pit with their guests making s’mores. Samantha and Brandon had a bonfire where they shared stories and memories while sipping on drinks. Brooke and Andy, who married at Brampton 1860, walked on the surrounding trails and played games with their guests before the wedding. Marisa and JC, who hosted their rehearsal dinner and welcome party at Herrington on the Bay, served pizza from a local brick oven pizza truck to kick off the festivities.
And after the final dance of the wedding, the weekend doesn’t have to end. After-parties and farewell brunches can end the weekend’s events on a high note. “It was such a nice way to see everyone off,” says Marisa and JC of their farewell brunch. “We were able to spend some more quality time with guests in a very laid-back setting.” Guests can stop in for a quick bite or a full sit-down breakfast, enjoying a final moment to celebrate the couple and spend time with loved ones.
Quality Time for Guests and the Couple
Getting a chance to talk to all of your guests the day of the wedding is a feat. But staycation wedding weekends make catching up more natural for both the couple and the guests. “It really allowed everyone to spend quality time together,” says Janeen and Todd. “Family members and friends who hadn’t seen each other in a while had time to reconnect.”
Since wedding weekend events are more casual, they’re ideal for meeting distant family members and plus-ones in a less formal setting. Conversations can be longer and deeper, allowing you to feel like you’ve connected and made memories with your guests. And it takes the pressure off having to greet everyone the day of the wedding.
“The truth is no amount of time with loved ones is ever enough,” says Brooke and Andy, “but we are so grateful for everyone pitching in and willing to stay the entire weekend with us to get in as much of those moments as we could!”
What to Look for in a Staycation Venue
First, look for estates and resorts that offer on-site accommodations. Depending on the size and your guest count, you may have just family and close friends staying on-site, or you may be able to get all guests to stay on the grounds.
Beyond spending time together, having guests stay on-site offers other benefits. “They loved being able to stay on the property and not have to worry about driving or [the] stress of finding somewhere to stay,” explains Samantha and Brandon.
Venues in or nearby small towns offer guests activities and places to explore during down-time. Quaint locations also provide a scenic backdrop to the weekend. Consider the amenities the venue has on-site as well. Pools, lawn games, and fire pits make great casual entertaining.
To get the staycation feel, book accommodations at the venue a few days before the wedding. The wedding party and close family can come those first few days before other guests. And as guests arrive, they’ll have plenty of relaxation and time to hang out before the big event.
A venue with a homey atmosphere is also a plus. “The way the Inn is situated makes for a neighborhood kind-of-feel,” says Marisa and JC about Herrington on the Bay, “so it was fun waking up, walking to breakfast and running into our family and friends on the way.”

